I'd give them the emoji keyboard on the login page. Make a web version they can use. The wider the possible keyspace the better.

We all know how great a company Apple is(sigh), but even they make mistakes. Stop defending stupidity just because it's Apple being stupid this time.

Don't get me wrong, it's a stupid limitation indeed -- but sometimes decisions like these are meant to stop users from doing stupider things :)

I'm no fan of oversimplification, but Apple's audience is everyone, not just power users. In that case, I'd prefer having advanced options surfaced to me as "advanced" so I can do what I want, but leave the simple experiences for the simple folk.